It has been known that a cyclic sulfonic acid ester (sultone) is a useful compound, for example, as an additive to non-aqueous electrolyte in a lithium ion secondary battery, which is capable of improving various battery characteristics. Specifically, it has been known that, for example, by adding an unsaturated sultone such as 1,3-propenesultone to non-aqueous electrolyte, not only an effect to suppress reductive decomposition reaction of electrolyte on a negative electrode can be expected, but also decrease of battery capacity in high-temperature storage test and cycle test can be suppressed, and gas generation associated with decomposition of electrolyte can be also suppressed (see, for example, Patent Literature 1 and the like). In addition, it has been also known that non-aqueous electrolyte containing, for example, hydroxysultone such as hydroxypropanesultone provides an effect to suppress decrease of charge and discharge efficiency which is significant in a lithium ion secondary battery, prolongation of cycle life, and an effect to suppress decrease of battery capacity (see, for example, Patent Literature 2, and the like).
As a method for producing an unsaturated sultone such as 1,3-propenesultone which is a kind of such cyclic sulfonic acid ester (sultone), specifically, for example, (1) a method where sodium allylsulfonate obtained by reacting allyl bromide and sodium sulfite is brominated to obtain dibromo-derivative thereof, subsequently cyclization reaction is carried out under acidic condition to obtain 2-bromo-1,3-propanesultone, thereafter dehydrobromination reaction is carried out to obtain the 1,3-propenesultone (see, for example, Non-Patent Literature 1 and the like), (2) a method where allylsulfonyl chloride obtained by reacting sodium allylsulfonate and phosphorous oxychloride is reacted with 1,3-dibromo-5,5-dimethylhydantoin to obtain 2-bromo-1,3-propanesultone, thereafter dehydrobromination reaction is carried out to obtain the 1,3-propenesultone (see, for example, Non-Patent Literature 2 and the like), (3) a method where 1,3-propanesultone is reacted with a halogenating agent in the presence of a radical initiator to obtain halogenated 1,3-propanesultone, thereafter dehydrohalogenation reaction is carried out to obtain the 1,3-propenesultone (see, for example, Patent Literature 3 and the like), (4) a method where allyl vinylsulfonic acid ester obtained by reacting vinylsulfonyl chloride and allyl alcohol is subjected to ring-closing metathesis in the presence of a ruthenium catalyst to obtain the 1,3-propenesultone (see, for example, Non-Patent Literature 3 and the like), and the like, have been known.
In addition, as a method for producing hydroxysultone such as 2-hydroxy-1,3-propanesultone, specifically, for example, (5) a method where sodium hydrogen sulfite prepared from sodium metabisulfite and sodium hydroxide is reacted with epichlorohydrin to obtain sodium 3-chloro-2-hydroxypropanesulfite, which is thereafter subjected to ring-closing reaction under heat condition to obtain the 1,3-propenesultone has been described (see, for example, Patent Literature 4 and the like).
However, in the above-described method (1), there are such problems that since all of bromine used to obtain 1,3-propenesultone become a waste, atom efficiency is poor, and that the step of dehydrobromination reaction carried out under a reduced pressure shows a low yield, and the like. When the present inventors actually implemented the method (1) in a commercial scale, 1,3-propenesultone as the target could not be obtained at all. Though detail is not clear, since the dehydrobromination reaction is carried out without using a solvent at a high temperature, it is considered that decomposition or gelation rather than the ring-closing reaction might occur in a commercial scale. In the above-described method (2), there are such problems that a substantial amount of expensive 1,3-dibromo-5,5-dimethylhydantoin has to be used, as well as that yield is low, and the like. In addition, in the above-described method (3), there are such problems that in the halogenation reaction of 1,3-propanesultone, 3-halogeno-1,3-propanesultone which is different in halogen substitution site is formed as a by-product, and since the 3-halogeno-1,3-propanesultone is not dehydrohalogenated and 1,3-propanesultone as the target is not formed, yield cannot be improved, and the like. Furthermore, in the above-described method (4), a comparatively expensive ruthenium catalyst has to be used, and hence the method can be hardly said as a commercial method.
In addition, when the present inventors traced the above-described method (5) disclosed as a method for producing 2-hydroxy-1,3-propanesultone, 2-hydroxy-1,3-propanesultone could not be obtained at all and presence of sodium 3-chloro-2-hydroxypropanesulfite as a synthetic intermediate could not also be identified. As a result of the study by the present inventors, it was found that sodium 3-chloro-2-hydroxypropanesulfonate instead of sodium 3-chloro-2-hydroxypropanesulfite had been formed. Thus, either methods have such problems that yield is low; a substantial amount of the comparatively expensive reagent has to be used; a cyclic sulfonic acid ester (sultone) as the target is difficult to obtain stably in a commercial scale; and the like, and are not necessarily advantageous method.
In such a circumstance, development of an efficient method for producing a cyclic sulfonic acid ester (sultone) as the target which is capable of not only using an economical raw material and a reagent but also synthesizing stably even in an commercial scale has been demanded.